[(1R,2S,3S)-1-cyclopropyl-4-ethoxy-2,3-dihydroxy-4-oxobutyl] 1,3-benzodioxole-5-carboxylate | 1393674-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: [(1R,2S,3S)-1-cyclopropyl-4-ethoxy-2,3-dihydroxy-4-oxobutyl] 1,3-benzodioxole-5-carboxylate
• CAS: 1393674-96-8
• 化学式: C₁₇H₂₀O₈
• 分子量: 352.341
• InChiKey: PLKVSHSBMSQHGN-SOUVJXGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  反式-4-氧基-2-丁烯酸乙酯 在 甲基磺酰胺 、 偶氮二甲酸二异丙酯 、 AD-mix β 、 三苯基膦 作用下， 以 四氢呋喃 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 3.0h， 生成 [(E,1S)-1-cyclopropyl-4-ethoxy-4-oxobut-2-enyl] 1,3-benzodioxole-5-carboxylate 、 、 、 [(1R,2S,3S)-1-cyclopropyl-4-ethoxy-2,3-dihydroxy-4-oxobutyl] 1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  Electronic helix theory-guided rational design of kinetic resolutions by means of the Sharpless asymmetric dihydroxylation reactions

  摘要：

  Kinetic resolution represents a key chemical reaction strategy for asymmetric synthesis of optically enriched compounds, and it originates from a simple phenomenon that a pair of mirror images (enantiomers) of a racemate can react with different rates under a chiral environment. While highly efficient catalytic kinetic resolutions by means of the classical Sharpless asymmetric epoxidation (AE) reactions are well established in modern organic synthesis, such systems based on the arguably more versatile Sharpless asymmetric dihydroxylation (AD) processes, although long pursued and widely attempted, remain largely underexplored. With insights gained from a new electronic helix theory we recently developed for molecular chirality and chiral interactions, we were able to advance a proposal suggesting why this problem is challenging and how it might be solved. Guided by a new design concept aimed at identifying complimentary catalyst-substrate electronic interactions, we reported herein that not only can such elusive systems be generally feasible, but efficiencies well reach the highest levels known to date with chemical or enzymatic kinetic resolutions of any type. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.06.102